Nevirapine (BioDeep_00000002098)

 

Secondary id: BioDeep_00000398961

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one

化学式: C15H14N4O (266.1167554)
中文名称: 奈韦拉平
谱图信息: 最多检出来源 Homo sapiens(blood) 2.24%

分子结构信息

SMILES: CC1=C2C(=NC=C1)N(C3=C(C=CC=N3)C(=O)N2)C4CC4
InChI: InChI=1S/C15H14N4O/c1-9-6-8-17-14-12(9)18-15(20)11-3-2-7-16-13(11)19(14)10-4-5-10/h2-3,6-8,10H,4-5H2,1H3,(H,18,20)

描述信息

Nevirapine is only found in individuals that have used or taken this drug. It is a potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV infection and AIDS. [PubChem]Nevirapine binds directly to reverse transcriptase (RT) and blocks the RNA-dependent and DNA-dependent DNA polymerase activities by causing a disruption of the enzymes catalytic site. The activity of nevirapine does not compete with template or nucleoside triphosphates.
J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AG - Non-nucleoside reverse transcriptase inhibitors
C471 - Enzyme Inhibitor > C1589 - Reverse Transcriptase Inhibitor > C97453 - Non-nucleoside Reverse Transcriptase Inhibitor
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D018894 - Reverse Transcriptase Inhibitors
D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents
D065693 - Cytochrome P-450 Enzyme Inducers > D065701 - Cytochrome P-450 CYP3A Inducers
D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
C254 - Anti-Infective Agent > C281 - Antiviral Agent

同义名列表

12 个代谢物同义名

2-cyclopropyl-7-methyl-2,4,9,15-tetraazatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-10-one; 11-Cyclopropyl-5,11-dihydro-4-methyl-6H-dipyrido(3,2-b:2,3-e)(1,4)diazepin-6-one; Hemihydrate, nevirapine; Nevirapine hemihydrate; ABBR NVP; nevirapine; BI-RG-587; BI RG 587; Viramune; BIRG587; NVP; NEV



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • Sharon Migeri, Muhammad A Lawal, Jeffrey Charles Hughes, Taruvinga Badza, Ovokeroye A Abafe, Bice S Martincigh, Alfred Oduor Odindo. Uptake of selected antiretrovirals by pepper (Capsicum annum), radish (Raphanus sativus), and ryegrass (Lolium perenne) grown on two contrasting soils and fertilized with human urine-derived fertilizers. The Science of the total environment. 2023 Jun; ?(?):164551. doi: 10.1016/j.scitotenv.2023.164551. [PMID: 37269997]
  • P N Kunene, P N Mahlambi. Case study on antiretroviral drugs uptake from soil irrigated with contaminated water: Bio-accumulation and bio-translocation to roots, stem, leaves, and fruits. Environmental pollution (Barking, Essex : 1987). 2023 Feb; 319(?):121004. doi: 10.1016/j.envpol.2023.121004. [PMID: 36608725]
  • Sa'ad T Abdullahi, Julius O Soyinka, Rahman A Bolarinwa, Olusola J Olarewaju, Alakija K Salami, Moji T Bakare-Odunola. Trough plasma nevirapine levels, immunologic and virologic responses in composite CYP2B6*6/*18 HIV-infected adult Nigerian patients. Basic & clinical pharmacology & toxicology. 2022 Jul; 131(1):45-52. doi: 10.1111/bcpt.13737. [PMID: 35484635]
  • Ceejay L Boyce, Tatiana Sils, Daisy Ko, Annie Wong-On-Wing, Ingrid A Beck, Sheila M Styrchak, Patricia DeMarrais, Camlin Tierney, Lynda Stranix-Chibanda, Patricia M Flynn, Taha E Taha, Maxensia Owor, Mary Glenn Fowler, Lisa M Frenkel. Maternal Human Immunodeficiency Virus (HIV) Drug Resistance Is Associated With Vertical Transmission and Is Prevalent in Infected Infants. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America. 2022 06; 74(11):2001-2009. doi: 10.1093/cid/ciab744. [PMID: 34467974]
  • Gentille Musengimana, Elysee Tuyishime, Athanase Kiromera, Samuel S Malamba, Augustin Mulindabigwi, Madjid R Habimana, Cyprien Baribwira, Muhayimpundu Ribakare, Savio D Habimana, Josh DeVos, Richard C N Mwesigwa, Eugenie Kayirangwa, Jules M Semuhore, Gallican N Rwibasira, Amitabh B Suthar, Eric Remera. Acquired HIV drug resistance among adults living with HIV receiving first-line antiretroviral therapy in Rwanda: A cross-sectional nationally representative survey. Antiviral therapy. 2022 06; 27(3):13596535221102690. doi: 10.1177/13596535221102690. [PMID: 35593031]
  • Monkgomotsi J Maseng, Leabaneng Tawe, Prisca K Thami, Sikhulile Moyo, Ishmael Kasvosve, Vladimir Novitsky, Max Essex, Gianluca Russo, Simani Gaseitsiwe, Giacomo M Paganotti. The role of CYP2B6 516G>T polymorphism on efavirenz/nevirapine toxicity. Implications on treatment outcomes: Lessons from Botswana. Medicine. 2022 Apr; 101(17):e29066. doi: 10.1097/md.0000000000029066. [PMID: 35512066]
  • Rosa Marlene Cuco, Osvaldo Loquiha, Adelino Juga, Aleny Couto, Bindiya Meggi, Adolfo Vubil, Esperança Sevene, Nafissa Osman, Marleen Temermam, Olivier Degomme, Mohsin Sidat, Nilesh Bhatt. Nevirapine hair and plasma concentrations and HIV-1 viral suppression among HIV infected ante-partum and post-partum women attended in a mother and child prevention program in Maputo city, Mozambique. PloS one. 2022; 17(2):e0261522. doi: 10.1371/journal.pone.0261522. [PMID: 35143515]
  • Musa Otieno Ngayo, Margaret Oluka, Wallace Dimbuson Bulimo, Faith Apolot Okalebo. Association between social psychological status and efavirenz and nevirapine plasma concentration among HIV patients in Kenya. Scientific reports. 2021 11; 11(1):22071. doi: 10.1038/s41598-021-01345-9. [PMID: 34764325]
  • Thaisa Cardoso de Oliveira, Antônia Carla de Jesus Oliveira, Yuri Basílio Gomes Patriota, Luise Lopes Chaves, Fabio de Oliveira Silva Ribeiro, Regina C M de Paula, Edson Cavalcanti Silva-Filho, Durcilene Alves da Silva, Mônica Felts de La Roca Soares, José Lamartine Soares-Sobrinho. Eco-friendly synthesis of phthalate angico gum towards nanoparticles engineering using Quality by Design (QbD) approach. International journal of biological macromolecules. 2021 Nov; 190(?):801-809. doi: 10.1016/j.ijbiomac.2021.09.012. [PMID: 34508723]
  • Bayazid Hassan Pour, Nahid Haghnazari, Fatemeh Keshavarzi, Elahe Ahmadi, Bahareh Rahimian Zarif. A sensitive sensor based on molecularly imprinted polypyrrole on reduced graphene oxide modified glassy carbon electrode for nevirapine analysis. Analytical methods : advancing methods and applications. 2021 10; 13(40):4767-4777. doi: 10.1039/d1ay00500f. [PMID: 34569556]
  • Gavin Bart, Le Minh Giang, Hoang Yen, James S Hodges, Richard C Brundage. Effect of HIV, antiretrovirals, and genetics on methadone pharmacokinetics: Results from the methadone antiretroviral pharmacokinetics study. Drug and alcohol dependence. 2021 10; 227(?):109025. doi: 10.1016/j.drugalcdep.2021.109025. [PMID: 34482033]
  • U M C Nibamureke, G M Wagenaar. Histopathological changes in Oreochromis mossambicus (Peters, 1852) ovaries after a chronic exposure to a mixture of the HIV drug nevirapine and the antibiotics sulfamethoxazole and trimethoprim. Chemosphere. 2021 Jul; 274(?):129900. doi: 10.1016/j.chemosphere.2021.129900. [PMID: 33979944]
  • C Zhou, S Liang, Y P Li, Y Yang, L J Liao, H Xing, Y H Ruan, D Yuan. [Influencing factors on the death of HIV/AIDS patients treated with antiviral treatment in Butuo county, Liangshan Yi Autonomous Prefecture, 2010-2019]. Zhonghua liu xing bing xue za zhi = Zhonghua liuxingbingxue zazhi. 2021 May; 42(5):886-890. doi: 10.3760/cma.j.cn112338-20200902-01115. [PMID: 34814483]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Theodore D Ruel, Edmund V Capparelli, Camlin Tierney, Bryan S Nelson, Anne Coletti, Yvonne Bryson, Mark F Cotton, Stephen A Spector, Mark Mirochnick, Rebecca LeBlanc, Christina Reding, Bonnie Zimmer, Deborah Persaud, Mutsa Bwakura-Dangarembizi, Kimesh L Naidoo, Rohan Hazra, Patrick Jean-Philippe, Ellen G Chadwick. Pharmacokinetics and safety of early nevirapine-based antiretroviral therapy for neonates at high risk for perinatal HIV infection: a phase 1/2 proof of concept study. The lancet. HIV. 2021 03; 8(3):e149-e157. doi: 10.1016/s2352-3018(20)30274-5. [PMID: 33242457]
  • David W Haas, Anthony T Podany, Yajing Bao, Susan Swindells, Richard E Chaisson, Noluthando Mwelase, Khuanchai Supparatpinyo, Lerato Mohapi, Amita Gupta, Constance A Benson, Paxton Baker, Courtney V Fletcher. Pharmacogenetic interactions of rifapentine plus isoniazid with efavirenz or nevirapine. Pharmacogenetics and genomics. 2021 01; 31(1):17-27. doi: 10.1097/fpc.0000000000000417. [PMID: 32815870]
  • Ha Young Yoon, Young Ah Cho, Jeong Yee, Hye Sun Gwak. Effects of CYP2B6 polymorphisms on plasma nevirapine concentrations: a systematic review and meta-analysis. Scientific reports. 2020 10; 10(1):17390. doi: 10.1038/s41598-020-74506-x. [PMID: 33060725]
  • S S Zulu, O Abboussi, N Simola, M V Mabandla, W M U Daniels. Anti-HIV drugs promote β-amyloid deposition and impair learning and memory in BALB/c mice. Acta neuropsychiatrica. 2020 Oct; 32(5):257-264. doi: 10.1017/neu.2020.19. [PMID: 32378496]
  • Lufuno Grace Mavhandu, Hua Cheng, Yeou-Cheng Bor, Denis Manga Tebit, Marie-Louise Hammarskjold, David Rekosh, Pascal Obong Bessong. Development of a pseudovirus assay and evaluation to screen natural products for inhibition of HIV-1 subtype C reverse transcriptase. Journal of ethnopharmacology. 2020 Aug; 258(?):112931. doi: 10.1016/j.jep.2020.112931. [PMID: 32360797]
  • HariOm Singh, Sonam Lata, Ranjana Choudhari, Tapan N Dhole. Prevalence of ABCC3-1767G/A polymorphism among patients with antiretroviral-associated hepatotoxicity. Molecular genetics & genomic medicine. 2020 06; 8(6):e1124. doi: 10.1002/mgg3.1124. [PMID: 32212330]
  • Chengbo Xu, Yijing Xin, Minghua Chen, Mingyu Ba, Qinglan Guo, Chenggen Zhu, Ying Guo, Jiangong Shi. Discovery, synthesis, and optimization of an N-alkoxy indolylacetamide against HIV-1 carrying NNRTI-resistant mutations from the Isatis indigotica root. European journal of medicinal chemistry. 2020 Mar; 189(?):112071. doi: 10.1016/j.ejmech.2020.112071. [PMID: 32004936]
  • Sa'ad T Abdullahi, Julius O Soyinka, Adeniyi Olagunju, Rahman A Bolarinwa, Olusola J Olarewaju, Moji T Bakare-Odunola, Markus Winterberg, Joel Tarning, Andrew Owen, Saye Khoo. Differential Impact of Nevirapine on Artemether-Lumefantrine Pharmacokinetics in Individuals Stratified by CYP2B6 c.516G>T Genotypes. Antimicrobial agents and chemotherapy. 2020 02; 64(3):. doi: 10.1128/aac.00947-19. [PMID: 31871092]
  • C R Kahlert, M Cipriani, P Vernazza. Novel dual HIV maintenance therapy with nevirapine plus lamivudine retain viral suppression through 144 weeks-A proof-of-concept study. PloS one. 2020; 15(9):e0237770. doi: 10.1371/journal.pone.0237770. [PMID: 32966293]
  • Juan Tiraboschi, Natalia Lattour, Hernando Knobel, Pere Domingo, Esteve Ribera, Daniel Podzamczer. Long-term efficacy and safety of nevirapine-containing regimens in virologically suppressed patients: a 17-year follow up. HIV research & clinical practice. 2019 12; 20(6):151-155. doi: 10.1080/25787489.2020.1724760. [PMID: 32065079]
  • Sipho Mdanda, Sphamandla Ntshangase, Sanil D Singh, Tricia Naicker, Hendrik G Kruger, Sooraj Baijnath, Thavendran Govender. Investigating time dependent brain distribution of nevirapine via mass spectrometric imaging. Journal of molecular histology. 2019 Dec; 50(6):593-599. doi: 10.1007/s10735-019-09852-w. [PMID: 31686324]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Rena C Patel, Randy M Stalter, Katherine K Thomas, Bani Tamraz, Steven W Blue, David W Erikson, Christina J Kim, Edward J Kelly, Kavita Nanda, Athena P Kourtis, Jairam R Lingappa, Nelly Mugo, Jared M Baeten, Kimberly K Scarsi. A pharmacokinetic and pharmacogenetic evaluation of contraceptive implants and antiretroviral therapy among women in Kenya and Uganda. AIDS (London, England). 2019 11; 33(13):1995-2004. doi: 10.1097/qad.0000000000002308. [PMID: 31306173]
  • Eliza D Hompe, Denise L Jacobson, Joshua A Eudailey, Kevin Butler, Whitney Edwards, Justin Pollara, Sean S Brummel, Genevieve G Fouda, Lameck Chinula, Melvin Kamanga, Aarti Kinikar, Dhayendre Moodley, Maxensia Owor, Mary Glenn Fowler, Sallie R Permar. Maternal Humoral Immune Responses Do Not Predict Postnatal HIV-1 Transmission Risk in Antiretroviral-Treated Mothers from the IMPAACT PROMISE Study. mSphere. 2019 10; 4(5):. doi: 10.1128/msphere.00716-19. [PMID: 31645430]
  • Valerie F Boltz, Wei Shao, Michael J Bale, Elias K Halvas, Brian Luke, James A McIntyre, Robert T Schooley, Shahin Lockman, Judith S Currier, Fred Sawe, Evelyn Hogg, Michael D Hughes, Mary F Kearney, John M Coffin, John W Mellors. Linked dual-class HIV resistance mutations are associated with treatment failure. JCI insight. 2019 10; 4(19):. doi: 10.1172/jci.insight.130118. [PMID: 31487271]
  • J Rueff, A S Rodrigues, M Kranendonk. A personally guided tour on some of our data with the Ames assay-A tribute to Professor Bruce Ames. Mutation research. Genetic toxicology and environmental mutagenesis. 2019 Oct; 846(?):503094. doi: 10.1016/j.mrgentox.2019.503094. [PMID: 31585631]
  • C Allavena, C Volteau, E André-Garnier, T Guimard, N Hall, L Khatchatourian, M Morrier, E Billaud, A Rodallec, V Reliquet, T Jovelin, L Le Guen, P Perré, M Grégoire, F Raffi. Switching from abacavir/lamivudine plus nevirapine to abacavir/lamivudine/dolutegravir in virologically controlled HIV-infected adults (SWAD study). Medecine et maladies infectieuses. 2019 Oct; 49(7):505-510. doi: 10.1016/j.medmal.2018.11.012. [PMID: 30583867]
  • Ahmad Haeri Mazanderani, Tanya Y Murray, Gayle G Sherman, Tracy Snyman, Jaya George, Theunis Avenant, Ameena E Goga, Michael S Pepper, Nicolette du Plessis. Non-nucleoside reverse transcriptase inhibitor levels among HIV-exposed uninfected infants at the time of HIV PCR testing - findings from a tertiary healthcare facility in Pretoria, South Africa. Journal of the International AIDS Society. 2019 06; 22(6):e25284. doi: 10.1002/jia2.25284. [PMID: 31215757]
  • Tavitiya Sudjaritruk, David C Boettiger, Lam Van Nguyen, Thahira J Mohamed, Dewi K Wati, Torsak Bunupuradah, Rawiwan Hansudewechakul, Penh S Ly, Pagakrong Lumbiganon, Revathy A Nallusamy, Moy S Fong, Kulkanya Chokephaibulkit, Nik K Nik Yusoff, Khanh H Truong, Viet C Do, Annette H Sohn, Virat Sirisanthana. Impact of the frequency of plasma viral load monitoring on treatment outcomes among children with perinatally acquired HIV. Journal of the International AIDS Society. 2019 06; 22(6):e25312. doi: 10.1002/jia2.25312. [PMID: 31179641]
  • Xiao-Lu Luo, Li-da Mo, Guo-Sheng Su, Jin-Ping Huang, Jing-Yu Wu, Han-Zhen Su, Wan-Hong Huang, Shun-da Luo, Zu-Yan Ni. Incidence and types of HIV-1 drug resistance mutation among patients failing first-line antiretroviral therapy. Journal of pharmacological sciences. 2019 Apr; 139(4):275-279. doi: 10.1016/j.jphs.2018.11.016. [PMID: 30928089]
  • Mehregan Safari, Mojtaba Shamsipur, Parvin Zohrabi, Homeira Ebrahimzadeh. Solid-phase extraction combined with dispersive liquid-liquid microextraction/HPLC-UV as a sensitive and efficient method for extraction, pre-concentration and simultaneous determination of antiretroviral drugs nevirapine, efavirenz and nelfinavir in pharmaceutical formulations and biological samples. Journal of pharmaceutical and biomedical analysis. 2019 Mar; 166(?):95-104. doi: 10.1016/j.jpba.2019.01.003. [PMID: 30639934]
  • Neda Hosseinpour Moghadam, Sadegh Salehzadeh, Jamshid Rakhtshah, Ashkan Hosseinpour Moghadam, Hamid Tanzadehpanah, Massoud Saidijam. Preparation of a highly stable drug carrier by efficient immobilization of human serum albumin (HSA) on drug-loaded magnetic iron oxide nanoparticles. International journal of biological macromolecules. 2019 Mar; 125(?):931-940. doi: 10.1016/j.ijbiomac.2018.12.143. [PMID: 30572041]
  • Sa'ad T Abdullahi, Adeniyi Olagunju, Julius O Soyinka, Rahman A Bolarinwa, Olusola J Olarewaju, Moji T Bakare-Odunola, Andrew Owen, Saye Khoo. Pharmacogenetics of artemether-lumefantrine influence on nevirapine disposition: Clinically significant drug-drug interaction?. British journal of clinical pharmacology. 2019 03; 85(3):540-550. doi: 10.1111/bcp.13821. [PMID: 30471138]
  • Suvaporn Anugulruengkitt, Tim R Cressey, Piyarat Suntarattiwong, Pradthana Ounchanum, Ussanee Srirompotong, Watsamon Jantarabenjakul, Jiratchaya Sophonphan, Yardpiroon Tawon, Sunti Punnahitanon, Chitsanu Pancharoen, Kulkanya Chokephaibulkit, Thanyawee Puthanakit. Nevirapine Concentrations During the First Month of Life and Maternal Efavirenz Washout in High-Risk HIV-Exposed Infants Receiving Triple Antiretroviral Prophylaxis. The Pediatric infectious disease journal. 2019 02; 38(2):152-156. doi: 10.1097/inf.0000000000002195. [PMID: 30204660]
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  • Seiji Kageyama, Alfredo Amolong Hinay, Elizabeth Freda Omengan Telan, Genesis May Jopson Samonte, Prisca Susan Agustin Leano, Akeno Tsuneki-Tokunaga, Kyosuke Kanai. Intrinsic Replication Competences of HIV Strains After Zidovudine/Lamivudine/Nevirapine Treatment in the Philippines. Journal of the International Association of Providers of AIDS Care. 2019 Jan; 18(?):2325958219856579. doi: 10.1177/2325958219856579. [PMID: 31216920]
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